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Picolyamine Based pH/Temperature Sensitive Hydrogels
Dai Phu Huynh,Cong Truc Huynh,이두성 한국고분자학회 2010 Macromolecular Research Vol.18 No.6
pH/temperature-sensitive hydrogels have attracted increasing attention as drug/protein delivery systems. This study reports a new pH sensitive moiety of picolyamine (PCA) and its pentablock copolymer hydrogels made from triblock PCL-PEG-PCL and picolyamine oligomer (OPCA). The picolyamine monomer (PCAM) was synthesized using the picolyamine and methacryloyl chloride coupling reaction. OPCA was synthesized by conventional radical polymerization from PCAM. The pKa of the pH sensitive moiety, OPCA, was found to be 6.65. The moiety was used to couple with PCL-PEG-PCL to produce the pentablock copolymer, OPCA-PCL-PEG-PCL-OPCA. The sol-gel phase transition of the aqueous solution of this material was affected by the pH and temperature change. In addition,the gel phase region could be controlled by the molecular weight of OPCA, the PCL/PEG ratio and chain length of PEG. This material could be used as an injectable hydrogel for drug/protein delivery.
Dai Phu Huynh,Minh Khanh Nguyen,이두성 한국고분자학회 2010 Macromolecular Research Vol.18 No.2
Poly (ethylene glycol) (PEG) - poly(ε-caprolactone(CL)-co-D,L-lactide (LA)) (PCLA-PEG-PCLA) was synthesized by ring-opening polymerization to form a temperature sensitive hydrogel triblock copolymer. Poly(β-amino ester) (PAE) obtained from 1,4-butanediol diacrylate (BDA), and 4,4'-trimethylene dipiperidine (TMDP) was used as a pH sensitive moiety to conjugate to the triblock copolymer. The physicochemical properties of the temperature-sensitive triblock and pH/temperature-sensitive pentablock copolymers (PAE-PCLA-PEG-PCLA-PAE) were characterized by 1H NMR spectroscopy and gel permeation spectroscopy. The sol-gel phase transition behavior of the PAE-PCLA-PEG-PCLA-PAE block copolymers was investigated. An aqueous solution of the copolymers (20 wt%) changed from a sol phase at pH 6.4 and 10 oC to a gel phase at pH 7.4 and 37 oC. In addition, the degradation of PAE-PCLA-PEG-PCLA-PAE was compared with that of poly(ethylene glycol) - poly(ε-caprolactone) - poly (β-amino ester) (PAE-PCL-PEG-PCL-PAE) using both in vitro and in vivo experiments. The relationship between the insulin release profile from the matrix and the degradation of these materials also investigated.
Biodegradable oligo(amidoamine/β-amino ester) hydrogels for controlled insulin delivery
Nguyen, Minh Khanh,Huynh, Cong Truc,Gao, Guang Hui,Kim, Ji Hyun,Huynh, Dai Phu,Chae, Su Young,Lee, Kang Choon,Lee, Doo Sung The Royal Society of Chemistry 2011 Soft matter Vol.7 No.6
<P>An injectable biodegradable hydrogel system based on oligo(amidoamine/β-amino ester) (OAAAE) was designed and synthesized for controlled release of insulin under the physiological conditions. OAAAE was prepared in one step <I>via</I> the Michael-addition oligomerization of the secondary aminegroups of 4,4-trimethylene dipiperidine (TMDP) with the vinyl groups of 1,8-octylene diacrylamide (ODA) and 1,6-hexane diol diacrylate (HDA). The formed oligomer was characterized by <SUP>1</SUP>H NMR and gel permeation chromatography (GPC). OAAAE in aqueous solution (20 wt%) underwent a gel–sol transition in the pH range of 6.8–7.4. A complex hydrogel was formed when mixinginsulin with the oligomer solution followed by increasing pH and temperature. Degradation of the hydrogel, influence of insulin on gel phase and gel strength, <I>in vitro</I> cytotoxicity of OAAAE, <I>in vitro</I> and <I>in vivo</I> release of insulin from the complex hydrogel were investigated. Furthermore, the <I>in vivo</I> release profile of insulin from the complex hydrogel was compared with that from the neutral hydrogel.</P> <P>Graphic Abstract</P><P>Controlled protein release using injectable and biodegradable oligomer hydrogel. <IMG SRC='http://pubs.rsc.org/services/images/RSCpubs.ePlatform.Service.FreeContent.ImageService.svc/ImageService/image/GA?id=c0sm01285h'> </P>
Thuy An Trinh,Thai Minh Duy Le,Hoang Gia Vinh Ho,Thi Cam Thach To,Vu Viet Linh Nguyen,Dai Phu Huynh,Doo Sung Lee 한국고분자학회 2021 한국고분자학회 학술대회 연구논문 초록집 Vol.46 No.1
Faculty of Materials Technology, Ho Chi Minh University of Technology (HCMUT)/Vietnam National University Ho Chi Minh City; <sup>1</sup>School of Chemical Engineering and Theragnostic Macromolecules Research Center, Sungkyunkwan University; <sup>2</sup>Vietnam National University Ho Chi Minh City/National Key Laboratory of Polymer and Composite Materials, Ho Chi Minh University of Technology, Vietnam National University; <sup>3</sup>Faculty of Materials Technology, Ho Chi Minh University of Technology (HCMUT)/ Vietnam National University Ho Chi Minh City/Research Center for Polymeric Materials, Ho Chi Minh University of Technology, Vietnam National University In this research, a novel insulin composite delivery system was prepared and characterized. Insulin drug was loading in chitoshan nanospheres using electrospraying method, a pH- and temperature-sensitive biodegradable hydrogel, which is an oligomer serine-poly(lactide)-poly(ethylene glycol)-poly (lactide)-oligomer serine (OS-PLA-PEG-PLA-OS) pentablock copolymer was used as a matrix to containing chitosan–insulin electro sprayed nanospheres (CIN). The properties of the OS-PLA-PEG-PLA-OS pentablock copolymer and the chitosan–insulin nanoparticles such as sol-gel transition, degradation in vitro and in vivo were characterized. The results showed that the chitosan–insulin nanospheres uniformly distributed in the matrix had a reinforcing effect on the mechanical properties and prolonged the degradation time of the hydrogel depot under body conditions. In addition, the cytotoxicity experiment results indicate that the composite could be used as a biomaterial for drug delivery system. The composite solutions accommodating different concentrations of the chitosan–insulin nanospheres were subcutaneously injected into induced diabetic BALB/c mice to study the in vivo insulin-release profile. The result showed that insulin concentrations in blood plasma were maintained at a steady-state level. Furthermore, the bio-properties of the insulin were retained and it showed a blood glucose level reducing effect for more than 60 hours after injection to a streptozotocin (STZ)-induced diabetic mouse model. The results suggested that this injectable pH–temperature sensitive hydrogel containing chitosan– insulin electro sprayed nanosphere composites has promising potential applications for type 1 diabetes treatment.